Apparel Spotlight

7 Hip-Hop Artists Who Headed Clothing Brands

7 Hip-Hop Artists Who Headed Clothing Brands

Mar 18, 2019

This article was originally featured on the City Gear blog in March 2018. Not all products in this collection are currently available on Last updated: January 21, 2020.

We all felt it when Jay-Z uttered those famous lyrics: “I’m not a business man; I’m a business, man!” and almost 20 years later in the age of side hustlin’, it still serves as a call to action to all who are determined to make it. As the old heads like to remind us, it is your talent that determines what you can do but your motivation that determines how much you are willing to do. This disciplined readiness always reveals the truly passionate business-minded ballers that have continued to seek out ways to get their recognition through diverse means. We know that in this industry, it is sink or swim, so we decided to give a lil’ shout out to those who took their elder’s advice to put their willingness to work. So, without further ado, here are a few examples of some of our favorite multifaceted megastars that have headed their own side hustle clothing brands:

1. AKOO/Hustle Gang T.I.

Created with the spirit of the hustle and remixed with upscale touches, AKOO and Hustle Gang, capture the echo of street culture and present it to the wider public in the form of contemporary streetwear suitable for every version of the urban gentleman. Refined and relaxed, who better to begin a brand than the king of class himself, Atlanta-based rapper T.I. Joined by his cofounder Jason Geter and armed with the mission to empower the those who come after them, the duo launched the twin lines with a fearless approach to fashion that shows through the meticulous use of bold colors and dynamic prints on every piece. Each garment holds its’ distinction from the rest through every inch of its’ high quality fabrication and smooth clean stitching to communicate the duo’s shared values of versatility,quick-wittedness, and independence.

2. Black PyramidChris Brown (a.k.a Breezy)

Founded by Grammy-award winning R&B singer Chris Brown, Black Pyramid expresses a quick-fire ready-for-anything attitude with its eccentric cut n’ sew detailing and premium fabrication. The streetwear line serves as an extension of the tastemakers of the world by acting as the next step in the evolution of urban style. It was made to be a representation of the global connection between varies elements of music, sport, art, and fashion while embodying all of the quirks and intricacies of various lifestyles and subcultures that define youthful happenings. Black Pyramid seeks to bring out a touch of self-admiration in its wearers, if only to be the marker of casual smoothness that is hailed by others.

3. Play ClothsPusha T

Founded in 2008 by Grammy nominated rapper Pusha T, the Virgina Beach-based streetwear brand Play Cloths helps its wearers stay youthful as the line seeks to evoke nostalgia from a simpler time of after school recreation in its adaptable lifestyle pieces. Luckily for us, childhood may be over, but playtime surely isn’t and Play Cloths’ use of bold graphics and one-of-a-kind color stylization influences the soul that sincerely yearns for amusement. Acting as an amalgamation of art, high-end fashion, and street culture, you can get it poppin’ in a variety of prints and pieces that help you get your grown man on while retaining all of the youthful characteristics that make you the authentic artist that you are. Its focus on high quality fabrication and an expression of individuality that makes Play Cloths equally for all work and all play.

4. Billionaire Boys ClubPharrell Williams

Vibrant, edgy, and full of life, Billionaire Boys Club got its start as one of the leaders of the boutique streetwear niche. Released in 2005, the line is a collab creation from American rapper/record producer Pharrell Williams and Japanese-designer, Nigo, the already famous founder of A Bathing Ape. The duo teamed up to produce chic garments that feature a tasteful blend of sharp graphics against high-quality cotton canvas for pieces that lie right at the intersection of cool and comfy. The line is known for its capsule collections that keep everything in limited quantities, so the wearer knows that their fit is always one-of-a-kind.

5. YeezyKanye West

All aboard the hype train! Anyone who has ever scrolled through Instagram or watched any episode of Keeping Up with The Kardashians knows about Yeezy. Originally associated with expensive ultra-hyped website-crashing adidas sneakers, the name now represents a larger lifestyle line that brings back the basics but with a new twist. Founded by the ever-changing rapper of the same pseudo name, the brand gives off a vibe of “utilitarian luxe” (whatever that is supposed to mean…). Unlike other streetwear collections, Yeezy’s consistent use of flat neutral colors gives off a subdued minimalistic vibe that is only broken up by the unusual sizing and extreme distressed detailing. While it may be out of many people’s price range, it serves its artistic purpose by accurately displaying Kanye’s vision that can only be described as controlled chaos.


Once the biggest player in the fashion game, NYC-based brand, ROCAWEAR, has left its mark on the world of urban fashion with its focus on the pulse of the Big Apple. ROCAWEAR is a multimillion dollar brand created by Damon Dash and the one and only, Shawn ‘Jay-Z’ Carter. The line originally started by exclusively selling streetwear, but after much success it expanded into other areas of outwear, loungewear, handbags, jewelry, and accessories. Its popularity came from not only the name recognition but from its ability to successfully pull trends from the NYC streets and export it to the world. The far-reaching garments don’t just sell the season’s latest styles but also sells an image in and of itself.

7. Sean JeanP.Diddy

Now seen as your uncle’s post-Thanksgiving meal fit, Sean Jean had its time in the limelight but continues to give us all a happy dose of nostalgia. Founded by rapper and business mogul, Sean John ‘P. Diddy’ Combs, the line got its start with smooth velour tracksuits and dynamic sportswear pieces, but it wasn’t long before it got enough love to warrant expansion into a full lifestyle brand. Its growing recognition got amplified after appearing on the runway of New York Fashion Week and earning Puffy the 2004 Men’s Designer of the Year Award. Today, that famous signature Sean Jean label can be found on everything from jeans, jackets, joggers, tees, and even formal menswear.